- Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 2: 4-Substituted 6-nitroquipazines
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Eleven 4-substituted derivatives of 6-nitroquipazine were synthesized and evaluated for their abilities to displace [3H]citalopram binding to the rat cortical synaptic membranes. Among them, 4-chloro-6-nitroquipazine was shown to possess the hi
- Se Lee, Byoung,Chu, Soyoung,Lee, Bon-Su,Yoon Chi, Dae,Song, Yun Seon,Jin, Changbae
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- Reactivity of Me-pma RhI and IrI Complexes upon Deprotonation and Their Application in Catalytic Carbene Carbonylation Reactions
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Dehydrogenative oxidation of amines is a relevant process in metal-mediated catalysis, with the amines being either substrates or ligands. Transformation of amine- into imine-type ligands in the coordination sphere of a transition metal can be an important catalyst activation process. The behaviour of secondary pyridin-2-ylmethanamine (pma) ligands in the corresponding rhodium and iridium complexes upon NH deprotonation varies, depending on a number of factors. In this paper the behaviour of the Me-pma ligand [Me-pma = N-methyl-1-(pyridin-2-yl)methanamine] bound to [Rh(cod)]+ and [Ir(cod)]+ was studied. Whereas the iridium amido complex could be obtained upon NH deprotonation, the rhodium complex instantaneously disproportionated into a free pma ligand and an unusual dinuclear complex, adopting a structure with two RhI metal centres hosted by a dianionic (pma-2H)2- ligand, and with the ligand coordinating to Rh2 as an "aza-allyl" fragment. The study gives further proof for the effect of pyridine ligation on the previously observed charge-transfer from the ligand to the metal. Furthermore, the catalytic activity of both the Ir and the Rh species with Me-pma in carbene carbonylation reactions to generate ketenes was studied.
- Tang, Zhou,Tejel, Cristina,Martinez De Sarasa Buchaca, Marc,Lutz, Martin,Van Der Vlugt, Jarl Ivar,De Bruin, Bas
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- Design, synthesis and molecular docking of substituted 3-hydrazinyl-3-oxo-propanamides as anti-tubercular agents
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Based on the anti-mycobacterial activity of various acid hydrazides, a series of substituted 3-hydrazinyl-3-oxo-propanamides has been designed. The target compounds have been synthesized from diethylmalonate using substituted amines and hydrazine hydrate
- Naqvi, Arshi,Malasoni, Richa,Srivastava, Akansha,Pandey, Rishi Ranjan,Dwivedi, Anil Kumar
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supporting information
p. 5181 - 5184
(2014/12/11)
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- Malonic ester amide synthesis: An efficient methodology for synthesis of amides
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A general methodology malonic ester amide synthesis has been demonstrated, which uses α-substituted/unsubstituted diethyl malonates for the decarboxylative acylation of various aromatic/heteroaromatic primary/secondary amines to form one-carbon homologated amides, thus providing easy access to amides with odd/even chain lengths and an array of substituents on the alkyl/aryl part while avoiding use of acyl chlorides or peptide coupling reagents. Copyright
- Mahajan, Pankaj S.,Mahajan, Jyoti P.,Mhaske, Santosh B.
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p. 2508 - 2516
(2013/07/25)
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- Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; A catalytic approach to ketenes
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One-pot radicals: Cobalt(III)-carbene radicals, generated by metallo-radical activation of diazo compounds and N-tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one-pot tandem transformations to produce differently substituted amides, esters and β-lactams in good isolated yields. Copyright
- Paul, Nanda D.,Chirila, Andrei,Lu, Hongjian,Zhang, X. Peter,Debruin, Bas
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supporting information
p. 12953 - 12958
(2013/10/01)
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- Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes
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The carbonylation of carbenes through catalytic cycles is highly desirable due to the importance of ketene-mediated reactions in organic synthesis. In this investigation, a highly efficient and mild catalytic approach toward ketene intermediates has been developed based on Pd-catalyzed carbonylation of diazo compounds with CO. When α-diazocarbonyl compounds or N-tosylhydrazone salts are heated in the presence of a palladium catalyst under atmospheric pressure of CO, ketene intermediates are formed in situ, where they undergo further reactions with various nucleophiles such as alcohols, amines, or imines. The Pd-catalyzed tandem carbonylation-Staudinger cycloaddition gives β-lactam derivatives in good yields with excellent trans diastereoselectivity. The results from DFT calculation on the reaction mechanism suggest that Pd is involved in the [2 + 2] cycloaddition process and affects the diastereoselectivity of the β-lactam products by assisting isomerization of the addition intermediate. On the other hand, the acylketenes generated from the Pd-catalyzed carbonylation of α-diazoketones react with imines in a formal [4 + 2] cycloaddition manner to afford 1,3-dioxin-4-one derivatives. This straightforward carbonylation provides a new approach toward highly efficient catalytic generation of ketene species under mild conditions.
- Zhang, Zhenhua,Liu, Yiyang,Ling, Lin,Li, Yuxue,Dong, Yian,Gong, Mingxing,Zhao, Xiaokun,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 4330 - 4341
(2011/06/21)
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- Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group
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A 2-nitrated 3-oxoester reacted with amines or alcohols to afford unsymmetrical malonic acid derivatives as a result of nucleophilic substitution accompanying C-C bond cleavage. The 2-nitrated 3-oxoester easily formed ammonium salts with amines. When the amine is liberated from the salt under equilibrium, nucleophilic amine and electrophilic keto ester locate close to each other. This intimate pair effect causes a pseudo intramolecular reaction to occur, giving rise to effective substitution under mild conditions.
- Nakaike, Yumi,Taba, Noriko,Itoh, Shinobu,Tobe, Yoshito,Nishiwaki, Nagatoshi,Ariga, Masahiro
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experimental part
p. 2413 - 2417
(2009/09/08)
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- Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines
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On the basis of the structure-activity relationship (SAR) of 4-chloro-6-nitroquipazine (Ki = 0.03 nM) and 3-fluoropropyl-6- nitroquipazine (Ki = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potenti
- Byung, Seok Moon,Byoung, Se Lee,Dae, Yoon Chi
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p. 4952 - 4959
(2007/10/03)
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